Perfluorinated allyl vinyl ethers have been described, for example in U.S. Pat. No. 4,337,211 that describes alkyl fluorocarbon ethers and methods for preparation thereof, and U.S. Pat. No. 4,358,412 that describes methods for preparation of alkyl vinyl ether monomers.
U.S. Pat. No. 5,264,508 describes polymers and copolymers prepared from diunsaturated mono- or poly-perfluoro or haloperfluoro ethers. One site of unsaturation is used in the polymerization, resulting in a melt-processable polymer. The second site of unsaturation is then available to crosslink the polymer giving a thermoset polymer. The copolymerization monomers said to be useful include "virtually any ethylenically unsaturated monomer capable of polymerization." (col. 5 lines 31-32). Phenyl and naphthyl radicals may be included in an ether used in the copolymerization, and these radicals may include substituent groups such as a halogen or --SO.sub.2 F.
U.S. Pat. No. 5,449,825 describes a method of preparation of perfluoro and haloperfluoro ethers, diethers and polyethers containing vinyl unsaturation, or allyl and vinyl unsaturation.
U.S. Pat. No. 5,023,380 describes compounds having two or more perfluorovinyl groups, along with their polymerization. Sulfur and sulfur-containing groups may be in the backbone of these materials. A hydrocarbyl group in the backbone must be either unsubstituted or inertly substituted, which is said to include sulfide, sulfoxide, and sulfone.
U.S. Pat. No. 5,066,746 describes a process of preparing tris-perfluorovinylether monomers.
WO 99/38842 describes perfluorovinylbenzene sulfonyl fluoride as a precursor to a polymer. It also describes polyimide-type aromatic polymers of sulfonated sulfone polyethers, and mono- and bi-functional monomers that can have sulfur-containing backbones or substituents.
WO 97/25369 describes several composite membranes that include various trifluorostyrene, substituted trifluorostyrene, and ethylene-based monomers.
WO 99/05126 describes perfluorovinyl ionic compounds and polymers made using them. The formulas described include perfluorovinyloxy substituents on a pentacyclic group and a backbone containing an aromatic group having one or more substitutents in addition to a sulfonyl group.
The polymerization of trifluorovinyl-containing monomers to form perfluorocyclobutylene polymers has been disclosed. For example, U.S. Pat. Nos. 5,037,917 and 5,066,746 describe a thermal process for preparing a polymer containing perfluorocyclobutane rings. The typical monomers described in these references have at least two dimerizable perfluorovinyl groups.